{(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Base Information

Chemical Name:{(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane
CAS No.:303727-91-5
Molecular Formula:C₂₃H₃₉BrO₃Si
Molecular Weight:471.55
Hs Code.:

Synonyms:{(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

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Chemical Property of {(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

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Technology Process of {(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

There total 13 articles about {(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

: 303727-90-4
Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

: 303727-91-5
{(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; benzene; for 1h;
DOI:10.1021/ja0015287

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 303727-91-5
{(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

2: 100 percent / DIBAL / tetrahydrofuran; hexane / 3.5 h / -78 °C

3: n-BuLi / tetrahydrofuran

With 2,6-dimethylpyridine; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; 1: silylation / 2: Reduction / 3: Condensation;
DOI:10.1021/ja0015287

Reference yield:

: 132969-71-2
methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

: 303727-91-5
{(Z)-(1R,2S)-4-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1.1: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

2.1: DMSO; oxalyl chloride; iPr₂NEt / CH₂Cl₂ / -78 °C

3.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - -8 °C

3.2: 63 percent / H₂O₂ / methanol / 10 h / 20 °C

4.1: AlMe₃ / tetrahydrofuran; hexane / 0 - 20 °C

4.2: 98 percent / tetrahydrofuran; hexane / 2.5 h / -20 °C

5.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

6.1: 100 percent / DIBAL / tetrahydrofuran; hexane / 3.5 h / -78 °C

7.1: n-BuLi / tetrahydrofuran

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Reduction / 2.1: Swern oxidation / 3.1: Evans aldol condensation / 3.2: Evans aldol condensation / 4.1: Metallation / 4.2: Substitution / 5.1: silylation / 6.1: Reduction / 7.1: Condensation;
DOI:10.1021/ja0015287